Sulphated amide wetting, detergent, and sudsing agents



Patented Aug. 8, 1944 SULPHATED AMIDE WETTING, DETERGENT, AND SUDSINGAGENTS Heinrich Bertsch, Rabenstein, near Chemnitz, Germany, assignor,by mesne assignments, to The Hydronapthene Corporation, Wilmington,Del., a corporation oi Delaware No Drawing. Application February 28,1939,

Serial No. 259,006

2 Claims. (Cl. 260-401) This invention relates to wetting, detergent andsudsing agents consisting of water-soluble salts of sulphuric acidesters of hydroxy allgvl, carboxylic acid amides and to a method wherebysuch agents may be directly and most efficiently produced. Agents forlike and related purposes composed of sulphuric acid esters of amides ofhigher fatty acid as a class, and also certain specific esters withinthe class, have already been patented to the applicant in the BertschPatent 1,918,373, dated July 18, 1933.

Agents similar to those of the present invention are already known tothe art, but those having compounds of unlike chemical structure areinferior in quality in the fields of use in which the instant agents areemployed, and those agents of the prior art having compounds of likechemical structure comprise mixtures with an ob ectionable proportion ofother compounds unavoidably or unintentionally present as a result ofthe specific method by which the agents have been produced, which mixedagents are poor in quality or efficiency as compared with the agents ofthe present invention.

Under the present invention, agents of the class herein described areproduced by a process wherein hydroxy alkyl, fatty acid amides of theproper molecular weight are prepared in a reaction wherein quantitativeyields are obtained, the resulting amides thereafter being sulphated andneutralized, thereby producing a product composed of substantially onehundred percent of water-soluble salts of sulphated hydroxy alkyl, fattyacid amides, which products constitute excellent wetting, cleaning andsudsing agents.

Outstanding features of the invention are the avoidance of hydrolysis ofthe product without using special conditions of treatment, such as lowtemperatures, thereby producing quantitative yields, and the greaterefflciency and extension in fields of use of the substantially pureproduct. The instant products are quite free of unreacted raw materials,intermediate and split reaction products, which products are present insimilar prior art agents.

In accordance with the preferred procedure of the instant process thechloride, bromide or other halide of fatty acids having 8 or more carbonatoms is reacted with hydroxy lower molecular aliphatic amines, and thehydroxy aliphatic radical, fatty acid amides obtained are thereafterreacted with sulphuric acid or other sulphating agent, after which theresulting acid ester is neutralized by means of sodium hydroxide orother base adapted to produce water-soluble salts.

The fatty acid halogenides used as the initial material in the presentprocess are derived in any suitable manner from the desired fatty acidor mixture of fatty acids having 8 or more carbon atoms in the molecule.These fatty acids may b either saturated or unsaturated fatty acids orhydroxy fatty acids. The fatty acid mixture obtainable from cocoanut oilis preferably used in the instant process, but the individual fattyacids may also be employed. Other suitable sources of fatty acidsinclude palm nut oil and sperm oil. Among the individual fatty acidssuitable for treatment, there may be mentioned lauric acid, myristicacid, palmitic acid, stearic acid, oleic acid and ricinoleic acid. Fattyacids of even higher molecular weight than in these examples aresuitable for the production of products for use in specific fie'lds, butfor general purposes the products derived from the carboxylic acidshaving from 8 to 18 carbon atoms give best results. Carboxylic acidsobtainable from oxidation products of hydrocarbons may be used inspecific instances, if such acids are obtainable in a sufficiently purecondition.

The amine component of the present invention is preferably a monohydroxyaliphatic amine of lower molecular weight. However, other hydroxy aminesmay be employed, such as, for example, monoalkylol amine, dialkylolamine and trialkylol amine. The alkylol radical may be either saturatedor unsaturated and the amine may be a mixed amine with alkyl radicalsdiflering in length of carbon chain. In the diand triamines, onesubstituent may be a hydroxy alkyl radical, whereas another may be aunsubstituted alkyl radical. Suitable alkyl radicals include ethyl,methyl, propyl and other lower molecular normal and isoalkyl radicals.The hydroxy aliphatic amines react readily with th fatty acidhalogenides, the reaction mass being preferably heated somewhat toincrease the rapidity of the reaction.

The sulphation of the hydroxy aliphatic, fatty The quantity of sulphuricacid employed dependsupon the nature of the raw material used and thenature of the final product desired. For example, when unsaturated bondsor more than one hydroxy group is contained in the hydroxy aliphatic,fatty acid amide, more than one sulphuric acid ester group may beintroduced into the molecule, in which case a larger quantity of thesulphating agent is employed. Furthermore, th sulphation reaction may becarried out in the presence of suitable solvents, including, forexample, lower molecular allwl ethers, such as ethyl, propyl and butylethers, pyridine and other tertiary bases. The use of these solvents isparticularly beneficial when unsaturated fatty acid radicals arecontained in the amide to be sulphonated and it is desired that a singlesulphuric acid ester group be introduced in place of the hydroxy radicalat the end of the alkyl chain.

Example 1 A fatty acid chloride mixture obtained from a commercialmixture of fatty acids derived from cocoanut oil, in a quantity of 245kgs. is mixed with 65 kgs. of monoethanol amine and caused to reacttherewith at slightly elevated temperatures. When the reaction has goneto completion, 275 kgs. of the resulting condensation product are thensulphated by the introduction of 300 kgs. of sulphuric acid monohydrateat room temperature. Thereafter the sulphated ethanol, fatty acid amidesare neutralized in conventional manner with sodium hydroxide.

Example 2 As in the foregoing example, the chlorides of cocoanut oilfatty acids are reacted with monoethanol amine. Thereafter 2'75 kgs. ofthe condensation product obtained are reacted with 120 kgs. ofchlorsulphonic acid in the presence of 200 kgs. of ethyl ether. Next thesulphuric acid esters obtained are neutralized with sodium hydroxide inconventional manner.

The sulphuric acid esters of the hydroxy aliphatic, fatty acid amides ofthe present invention are preferably employed in the form of theirwater-soluble salts. For obtaining these salts, the alkali metalhydroxides and other inorganic bases are suitable. Also, organic basesmay be employed for the neutralization, compounds such as triethanolamine and triethyl amine bein8 satisfactory. The organic salts areparticularly useful in the production of cosmetics, shampoos and thelike.

As hereinbefore indicated, the products of the present invention aregenerally useful as wetting, detergent and sudsing agents. They may beemployed to advantage in household operations and in industrialprocesses of the most varied nature.

They are useful as assistants in the textile. leather and alliedindustries, also in the pharmaceutical industry and in the preparationof insecticides.

Although the compounds of the present invention may be satisfactorilyused in the absence of additional capillary active or other agents, suchcompounds may, for the preparation of products for specific purposes, beadmixed with other substances of the nature of soaps, higher molecularalcohols, ketones, aromatic sulfonic acids and their salts, sulfonatedoils, and organic solvents, including hydrocarbons and halogenderivatives of hydrocarbons.

- The outstanding advantage of the present in- .vention, as hereinbeforeindicated, lies in the simplicity and efl'ectiveness of the processsteps involved, whereby substantially one hundred percent of the organiccompounds employed combine in the reaction to form the desired product.

Therefore, the product is obtained in a state free from other similarreaction products, such as alkylol amine esters of fatty acids, whichare lower in efficiency or do not possess the valuable properties of thewater-soluble salts of the sulphuric acid esters of the hydroxy alkyl,fatty acid amides. The product is, for example, free of any hydroxyalkyl amine ester of fatty acids either in its free or sulphated form,which products have been present in similar agents prepared inaccordance with prior art processes.

It should be understood that the present invention is not limited to thespecific substances described or the specific procedure disclosed, butthat it extends to all other compounds and equivalent procedures withinthe scope of the claims appended hereto.

I claim: 1

1. The process of directly producing watersoluble salts of sulphatedhydroxy alkyl, fatty acid amides in a form substantially free ofextraneous organic materials, which comprises condensing amonohaloge'nide of a fatty acid containing at least 8 carbon atoms witha lower molecular monoalkylol amine, thereby obtaining a quantitativeyield of a hydroxy alkyl, fatty acid amide, then sulphating said productat the said hydroxy group and neutralizing to produce a water-solublesalt of the sulphuric acid ester of said amide.

2. The process of producing wetting, detergent and sudsing agentsconsisting of water-soluble salts of sulphuric acid esters of hydroxyethyl, acyl amide, said acyl group having 8 to 18 carbon atoms, whichcomprises condensing a carboxylic acid monochloride having 8 to 18carbon atoms with monoethanol amine, sulphating the reaction product atthe said'hydroxy group and neutralizing with a base adapted to form awater-soluble salt of the sulphuric acid ester formed.

- HEINRICH BERTSCH.

